Motivation
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I think new technology seems to be driving the changes in managerial roles and skills. This is because more advance technologies have been introduced in past 20 years and that have derived customers with competitive problems and requirements. These new requirements are not easy to develop with previous organization structures.
The job environment and requiring additional communications and skills is also changed in 20 years. There was minimal diversity and all the work was done in United States. Now, there is more diversity and most of the work is outsourced to other countries. Todays managers have to adopt this new changed environment to be successful and effective. I would have to say that the concept and responsibilities didnt change a lot except methods. They still have to deliver system on time, within budget, and etc.
I think it depends on what kind of negative personality traits he possesses. If they are related to any managerial roles and responsibilities and it will affect the team down the road then it is not a good idea to give him a promotion into a management position. If they are not related to any managerial roles and it will not affect the team then he should be given a chance to become a manager. May be by doing this he will improve his bad habits and become a successful manager. On the other hand he should be recognized for his hard work by either giving him a raise or bonus.
Motivation changes depend on the individuals personal life and career phase (as well as many other circumstances and values).
In Bobs case, having a role in the organization that is rewarding and a good relationship with his boss and having that boss care enough to coach and promote his career is a primary motivation.
The motivation factors might change when he looks to apply for a loan to buy a house, when salary can become